11,047 research outputs found

    Dienes, Louis -- 1939-42 -- Correspondence, Individual -- letter, 1941-10-17

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    Letter from Dienes, Louis to Sabin, Albert B. dated 1941-10-17.Sabin Collection Fair Use Policy</a

    Dienes, Louis -- 1939-42 -- Correspondence, Individual -- letter, 1939-06-02

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    Letter from Dienes, Louis to Sabin, Albert B. dated 1939-06-02.Sabin Collection Fair Use Policy</a

    Organolanthanide-Catalyzed Cyclization/Boration of 1,5- and 1,6-Dienes

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    1,5- and 1,6-Dienes undergo a cyclization/boration reaction in the presence of a catalytic amount of Cp*2Sm·THF. The resulting organoboranes can be oxidized to the corresponding primary cyclic alcohols using standard conditions

    A Dual CuH- and Pd-Catalyzed Stereoselective Synthesis of Highly Substituted 1,3-Dienes

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    Conjugated dienes are versatile building blocks and prevalent substructures in synthetic chemistry. Herein, we report a method for the stereoselective hydroalkenylation of alkynes, utilizing readily available enol triflates. We leveraged an in situ-generated and geometrically pure vinyl-Cu­(I) species to form the Z,Z- or Z,E-1,3-dienes in excellent stereoselectivity and yield. This approach allowed for the synthesis of highly substituted Z-dienes, including pentasubstituted 1,3-dienes, which are difficult to prepare by existing approaches

    Visszatekintés : Életmű interjú Dienes Istvánnal

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    Dienes István szakmai életútja, amely a mérhető információgazdaság megfogalmazásáig vezette

    Copper-Catalyzed Asymmetric Reductive Allylation of Ketones with 1,3-Dienes

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    A catalytic chemo-, regio-, and enantioselective allylation of ketones with 1,3 dienes in the presence of (R,R)-Ph-BPE ligated Cu catalyst and hydrosilane is presented. This method provides a straightforward and alternative avenue to synthesize chiral homoallylic tertiary alcohols with 1,3-dienes as the latent allylic nucleophiles and avoids the traditional reliance on stoichiometric quantities of allylmetal reagents. This transformation proceeds under very mild conditions and displays good functional group tolerance and could be performed on a gram-scale

    Rhodium-Catalyzed Hydrofunctionalization: Enantioselective Coupling of Indolines and 1,3-Dienes

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    We communicate a strategy for the hydrofunctionalization of 1,3-dienes via Rh-hydride catalysis. Conjugated dienes are coupled to nucleophiles to demonstrate the feasibility of novel C–C, C–O, C–S, and C–N bond forming processes. In the presence of a chiral JoSPOphos ligand, hydroamination generates chiral allylic amines with high regio- and enantioselectivity. Tuning both the pKa and steric properties of an acid-additive is critical for enantiocontrol

    Photoinduced, Palladium-Catalyzed Enantioselective 1,2-Alkylsulfonylation of 1,3-Dienes

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    The chiral allylic sulfonylated group is a unique structural motif embedded in a range of natural products and pharmaceuticals. Notably, the synthesis of structurally diverse chiral allylic sulfonylated derivatives via alkylsulfonylation of 1,3-dienes remains underexplored because of its inherent challenges in stereocontrol and regioselectivity. Herein, photoinduced, palladium-catalyzed enantioselective 1,2-alkylsulfonylation of conjugated 1,3-dienes is described. A wide variety of alkyl bromides, 1,3-dienes, and sodium sulfinates could be facilely coupled to generate value-added chiral allylic sulfonylated derivatives with high enantioselectivity. Finally, the utility of this enantioselective difunctionalization protocol was demonstrated in pharmaceutical analogue synthesis

    The rearrangement of alkylallenes to 1,3-dienes

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    1,3-Dienes are vital building blocks in organic synthesis. They underpin many fundamental synthetic transformations and are present in numerous natural products and drug candidate molecules. The rearrangement of an alkylallene to a 1,3-diene is an atom efficient, redox neutral, transformation that provides a straightforward synthetic route to functionalized 1,3-dienes. Herein, we provide an account of this transformation using allenes that are not predisposed by the presence of heteroatoms or electron-withdrawing groups directly attached to the allene. Early reports of this skeletal rearrangement are acid-mediated approaches, with limited substrate scope, but they provide valuable mechanistic insights. More recent transition metal-mediated approaches that exhibit improved substrate scope are described, together with isolated examples that have utilized this rearrangement

    Cu-Catalyzed Enantioselective Protoboration of 2,3-Disubstituted 1,3-Dienes

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    A Cu-catalyzed regio- and enantioselective protoboration of 2,3-disubstituted 1,3-dienes is described. The protocol operates under mild conditions and is applicable to symmetrically and unsymmetrically substituted dienes, providing access to homoallylic boronates in consistently high yield, regioselectivity, and enantiomeric ratio. Preliminary investigations point to a complex mechanism
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